Teaching Stephanie Pt. 01

Eric looked at his watch and wondered how long it was going to take her. She must be looking herself over in the mirror or else she really had had to pee that badly.

He was sitting in an empty library with schoolwork spread out all over the desk in front of him. Incredibly easy schoolwork, he thought to himself, for anyone with half a brain. But then again, that was why her parents had paid him to tutor her. Stephanie Chen's parents were a stereotypical Asian power couple, Mr. Chen was a doctor and Mrs. Chen was a corporate manager or something. It bothered them to no end that their daughter Stephanie was only an average student much more interested in dating and partying than in preparing for college.

Not that Eric was really preparing for college either. He had started helping other kids with college exams in his junior year and by the next he had started charging for it. After graduation he had decided that spending a gap year extorting money out of concerned parents would be much more fun than sitting through freshman classes he already knew the material for and would earn him a nest egg for when he did end up going. For now though, there was still the issue of Stephanie, gone for over five minutes after she said she had to use the bathroom.

As he looked around, bored, there was suddenly a small ding which made him jump nearly halfway out of his seat. He had been so dazed and day-dreamy he was surprised by what was clearly a message tone. He glanced at the desk and saw she had left her phone. Glancing around some more, he didn't see her on her way back yet, so out of boredom and curiosity he picked it up.

The screen showed she had gotten a text from someone named "Teddy". Must be her boyfriend, though he'd have to be as much of an airhead as her he snickered. Then he noticed that her screen wasn't password protected. Checking once more to make sure he was still alone he whispered "Let's see what Teddy wants?" under his breath and swiped it open. His boredom quickly disappeared as he realized he had just stumbled into reading what was a quite explicit sext session. She had three pictures of herself on there, one bent over and showing her bare ass to what appeared to be her bedroom mirror, another from the other angle showing her small tits and shaved pussy, and a final one with her using a small pink vibrator on herself, legs spread apart.

Oh man! he thought, this is fucking gold! In a hurry he forwarded the whole conversation along with the pictures to his number and replaced her phone where it had been. What kind of idiot has pictures like that on her phone and doesn't even have a password on it he wondered. He only had about another minute to digest what he had just seen when Stephanie sauntered back over and plopped herself back down in her seat. He watched as she settled herself and got back to work on the papers in front of her. He continued to eye her over as he began once more to assist her with the problems she found difficult.

He had looked at her once or twice before and noticed she was kind of cute, but now he looked more intently. She was small, with dark hair and dark eyes. Her breasts and ass were kind of small too, but in that still slightly curved, petite Asian sort of way. She was fit and always done up, of course she was she was a cheerleader. Not the most popular or the hottest, but definitely part of that crowd. It wouldn't surprise him at all to find out that Teddy was a football player and they were a cliché couple.

Then he started to imagine what all Teddy had gotten to experience though, based off of the few texts he had had time to skim over. He was having trouble staying focused as he imagined what it would be like to have her sending him pictures like that, of watching her masturbate and tell him all the dirty things she wanted to try with him. At this point his dick was so hard he was grateful it was hidden by the desk. After just a few more minutes of distracted work he told her to go on home early, that he had errands to run. In reality he just wanted to get home as fast as he could so that he could continue working on a plan he already had forming.

**************

Two nights later they were back at the library. He was there early, as usual, but this time he was actually anxious for her to show up. He had decided to try and leverage his windfall into something fulfilling, rather than just saving it as jerk off material, but it remained to be seen how she would react.

As he turned around he saw her walk in. She usually came straight from cheerleading practice in skimpy workout outfits and today was no exception. She was wearing spandex short shorts that clung to her butt and thighs, outlining what small curves she did have. Her top was simply a cut up t-shirt he could clearly see a sports bra through. Her hair was pulled up in a messy bun, her skin glistened with sweat. She took off her backpack and sat down beside him, he began to get more nervous as she pulled out her books, what if she didn't react well to him trying to blackmail her? After all this was real life not some porn flick.

"What are we working on today?" she asked, all of her books spread out and opening her notebook. "Well about that Stephanie", he started, "there's something we have to talk about first." She looked at him with confusion on her face. "About what?" He cleared his throat and continued "About me tutoring you, you see, I don't think I can tutor you any longer." "I don't understand" she said, "What happened?

This was his moment. "Well you see, last time when you left to use the bathroom you forgot your phone and while you were out you got a message." He looked at her but she was just staring back at him, seeming tense. "I read the message, messages in fact, and realized that I just don't feel like I'm being paid appropriately to teach a girl who would do things like you have just to get yourself tickets to a concert." That had been in there after he had gotten home and read them fully. Teddy wasn't her boyfriend, just some guy who had backstage tickets to an artist she had wanted to see. That was what had convinced him this plan might work, the girl was obviously enough of a slut that it could.

"So, what?" she cut in, "You expect me to have sex with me just because you know that I sent some guy a nude pic or two?" "No," he said firmly, "I expect you to have sex with me because I have copies of the pictures, and the messages and I don't think you want your parents to see them." By this time she was clearly mad, but holding it in, knowing there wasn't much she could do. "How can I trust you though?" she asked with a hint of anger and a hint of desperation in her voice. "If you do have pictures what's to stop you from showing my parents anyways? For that matter I don't even know for sure you have any copies at all! My parents would be pissed but I didn't fuck the guy or anything so eventually they'll get over it. Maybe I should just go tell them myself like I'm sorry I messed up and then report you for invading my privacy, underage porn or whatever!" As she reached the end of her tirade she was moving to grab her bag and leave.

"First" he got out, quickly taking his phone from his pocket and showing her the evidence. "Because you now know that I do have them." He put his phone back. "Second, because before you could report me I could have them wiped off anything that's mine and send the police an anonymous tip that "Teddy" is soliciting 18 year old girls for sexual favors. He has copies too or did you not think of that? And third, because it wouldn't just stop at your parents. What do you think school will be like once everybody finds out how much of a whore you are? Or how many colleges will accept you no matter how well you do on your exams if they also know you give it up to anybody with something you want in return? Then again, the professors might feel like it's a dream come true, a slutty 18 year old willing to put out for a little consideration in grading maybe? Of course that might not all be true but people will think it is and that's what matters."

As Stephanie's understanding of just how bad her situation was fully sank in most of the rage in her eyes melted away and was replaced by panic. She now seemed almost ready to break into tears, the instinct to fight had kicked in first and now she was turning to flight, unfortunately for her there was nowhere to run. Slowly she hung her head and dropped her bag on the floor, crossing her arms and feet. "So how does this work, you said I do have to fuck you?" She asked, still with a trace of resentment.

Finally Eric had her where he wanted her, vulnerable and realizing full well that this was something she was going to have to do if she had any hope of it not ruining her life. "Three times. After each time I'll let you personally delete one photo from my phone. You'll just have to take my word for it that I don't have it stored somewhere else too." Eric gloated inside, maybe this was like porn, it was certainly better than any real experience he had had so far.

"Okay but, look the thing is..." she was the nervous one now, fidgeting and looking around like there were other people there who might be listening to the conversation. "I've never had sex okay? My parents won't let me take the pill so that I won't. So how about I blow you, huh? Three blowjobs for three pictures sounds fair right?" Her tone no longer held any resistance, just hopefulness that this would soon be behind her.

He put his hand on his chin and tried to appear like he was considering the offer. It wasn't much of a choice really, he loved blowjobs more than actual sex really, and she had just offered to do it all three times. He just needed her to know that this wasn't a negotiation, she would do what he wanted.. "That's fine" he said. "Three times having oral sex when I say and how I say. That will get you in the clear." He saw her visibly relax a little bit, relieved that he wasn't going to split her virgin pussy wide open. "Tomorrow," he continued, "is the first time. This is my address. Show up at the normal time we'd be here. Oh and, show up in your cheerleader uniform. I have the house to myself so don't worry about being seen by anybody." He slid over a slip of paper and got up to walk out. "Be on time."

**************

Eric walked down the stairs as the doorbell rang, glancing at a clock on the wall. She was actually on time, five minutes early to be precise. Maybe she's gonna take this seriously he thought. She had never shown up to a tutoring session on time. He opened the door and Stephanie was standing behind it.

The cheerleader uniform was black with white trim which matched with her long black hair, pulled up in a ponytail, and white socks and sneakers. He realized when they were standing just how petite she was, he was just under six feet tall but she couldn't possibly be much taller than five feet tall even with the shoes on. Her hands were on her hips and he doubted she could look more impatient if she tried. "Well are we just going to stand here all day or are you gonna let me in before people think it's Halloween and I'm trick-or-treating?"

He swung his arm out as he moved to the side, motioning her in. He shut the door behind her and said "My room's up the stairs, second on the right." He made sure to walk a few steps behind her so he could watch her tiny ass bounce back and forth, as well as just a hint of what lay underneath the skirt. They rounded the corner into his room and she turned as soon as she could saying "Come on, let's get this over with."

"Not so fast" Eric replied, "You need to change your hair, I want it in pigtails." She actually smirked at him, before she came back with "Pigtails, isn't this already cliché enough with the uniform? Besides, I don't have any extra hair ties". Eric pointed down the hall "My sister's room was the first one, she'll have some in there, and we did agree on how I want or no pictures." She put on a pouty look as she moved back down the hall. She was only gone for two minutes before she reappeared, two pigtails on the sides of her head. She closed the door behind her. "Okay, now let's get this over with.

Eric pulled his shirt over his head and dropped his pants in two smooth movements. He looked back at Stephanie and saw her eyes widen slightly in surprise. Eric knew she hadn't expected him to look like he did. Because he was a smart kid, a nerd, and had never been in any school sports people always assumed he was like most other nerds; isolated video game players who were either fat or scrawny. Even though he'd never bee an athlete he was fit, he ran, hiked, surfed, rock climbed and a million other things besides. His skin was tanned from time outside and his muscles were lean, showing clear lines on his chest and arms and hints of abs on his torso. His hazel eyes matched neatly with his brown hair, slightly sun-bleached. Stephanie was even biting her lip slightly like she might enjoy this more than she expected.

"On your knees" he told her, and she complied, getting down to her knees and scooting up a little in order to position herself closer to him. She reached up with both hands and peeled his underwear down and over his his legs while he stepped out. Her eyes widened again and again he understood why. Eric was only an average six inches long but he had the girth of a cock much larger. She must be wondering if she could open her mouth wide enough to even fit it in. Maybe even some further relief over the fact he would only be using her mouth and not her tight little pussy.

"Open your mouth, stick your tongue out." He continued to direct her. She did as he said, settling her butt back on her heels, hands on thighs and looking up at him with her mouth waiting. He grabbed his dick which had been at full size already from the anticipation at the base and began tapping the head lightly against her wet tongue. He tapped it a few more times, getting faster. "Have you ever sucked a dick before?" He asked as he looked down at her. She nodded twice, keeping her tongue out as he continued to tap his against it. "Of course you have you little slut." He put his hand on her head and pushed her mouth down on his balls and continued tapping, now on her forehead.

She began to slowly suck his left testicle in and almost out, moving her head a little to mimic the motion. "How many?" he asked, knowing it had to be more than one. She let go of his ball with a little popping sound and reached up to start stroking his dick as she said "Two", then turned her eyes back down and resumed sucking on his balls, only now with her hand moving its way up and down his thick shaft. Eric looked up at the mirror on the back of his door to watch her bobbing and jerking from a different angle. His gaze moved downwards to the base of her skirt, which currently sat just low enough to hide what he really wanted to see.

He took a step back and told her to get down on all fours. She leaned forward and put her hands on the floor, getting that perfect dip in her back that placed her ass high in the air and now clearly in view in the mirror. Her round cheeks were hidden behind a tight pair of white cotton panties which also obscured his true goal. He reached over and pulled them down to around her knees, now he could see her full cheeks, puckered asshole and full lips. He stepped back again and got down to his own knees, hard cock dangling just inches from her face.

To her credit, she didn't need him to tell her what to do at this point and immediately took it in her mouth. Just as he had thought he was so wide he barely fit inside, but still, it was as warm and wet as he could have hoped. She compensated for not being able to slide very much in by creating even more suction around what she could. He alternated his view between looking straight down at her lips wrapped around his cock and the mirror, watching her ass and pussy bounce forwards and backwards.

Eric reached down and grabbed a pigtail in each hand and pulled towards himself, exerting a light but steady pressure, gaining him maybe an extra inch, his dick now sliding just more than halfway in. He also began to slowly thrust his hips, each time her mouth enveloping his cock just a little bit more. Bit by bit he picked up speed, faster and faster until he was pumping her face, she started to make little gagging noises and he could see tears starting to fall from at least one eye from the strain of holding her mouth open that wide for that long.

He glanced at the top of her head as he asked "Did you spit or swallow with the other two?" She couldn't truly speak with his cock relentlessly searching for the back of her throat, but managed to mumble something that sounded like "spit" out. He dropped the pigtails and placed both hands on the back of her head and told her "Well you're going to swallow today." She squeaked and tried to shake her head, scooted her knees in and placed her hands on his thighs in an attempt to push away. Futilely, because his arms were too strong. He held on as she struggled, now furiously thrusting away and getting closer to cumming, he could feel his cock starting to pulse, ready to explode.

He felt the vibrations and then suddenly his cum was gushing out, as he held her down, her lips almost to the base of his cock. She continued to make noises of protest as the next few squirts shot more still. Finally after several more convulsions he felt spent, his balls completely drained. His dick was already going soft after such a hard fuck so he went ahead and pulled it out.

"Open your mouth" he barked, "I want to see it, I want to see my cum in that mouth." She opened it up, his cum pooled at the back of her tongue. "Now swallow slut!" He waited as she slowly closed her mouth and hesitantly gulped down the large load. "Open it again, stick your tongue out." He squeezed his penis, milking every little bit left inside out to the tip of his head and wiped it on her tongue. "Every last drop" he said.

She swallowed that too and then sat back, staring up at him, face streaked and panties still pulled down. He swaggered over to his bed and grabbed his phone, bringing it back over and opening it up to his gallery. He let her delete the photo that showed her ass, just like he had been looking at in the mirror, and then grabbed hi phone back quickly before she could get the rest, tossing it back onto the mattress.

Suddenly he reached down and slid her panties down past her ankles before she could stop him. She yelled "Hey" and got up to do something about it but he pushed her back towards the door, opened it, and pushed her out the rest of the way, hurriedly closing it behind her. She started to yell louder and bang on the door while he stood there naked, limp, and panties in hand. He had plans for them later. "Go home" he yelled back a the other side of the door. "I'll see you again in two days."

After a few minutes the pounding stopped and he walked over to his desk where his laptop sat open, webcam turned on. She had never even glanced that way, to see the light that said it had been recording before they even entered the room. Of course she might think she was getting rid of the evidence of her sexual escapades, but of course he wouldn't be stupid enough to leave himself without anything..

Chuckling as he stopped the recording he rolled the white panties over in his fingers as he mused once more over his next steps. Oh he had plans indeed for Stephanie Chen and her mouth...